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Stereospecific Pd‐Catalyzed Intermolecular C(sp 3 )–C(sp) Cross‐Coupling of Diarylmethyl Carbonates and Terminal Alkynes Under Base‐Free Conditions
Author(s) -
Tabuchi Sho,
Hirano Koji,
Miura Masahiro
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503647
Subject(s) - stereocenter , intermolecular force , stereospecificity , catalysis , chemistry , base (topology) , palladium , coupling (piping) , stereochemistry , organic chemistry , enantioselective synthesis , molecule , materials science , mathematical analysis , mathematics , metallurgy
A palladium‐catalyzed intermolecular decarboxylative C(sp 3 )–C(sp) coupling of diarylmethyl carbonates and terminal alkynes has been developed. The reaction proceeds smoothly under external base‐free conditions to deliver the corresponding alkynylated diarylmethanes with the liberation of CO 2 and MeOH as the sole byproducts. Moreover, enantioenriched diarylmethyl carbonates are stereospecifically converted to optically active cross‐coupling products with inversion of configuration. Thus, the stereospecific palladium catalysis can provide new and unique access to the alkynylated chiral tertiary stereocenters, which are relatively difficult to construct by conventional methods.